In righteously progressive San Francisco, the two-term mayor who calls himself a “pro-business Democrat” has been slammed as too conservative, even as he grappled creatively with chronic homelessness, signed into law the city’s groundbreaking universal healthcare program and even helped make composting compulsory. Everywhere else, though, he’s the liberal who rubbed the nation’s nose in gay marriage.

Now, as the 43-year-old finds himself in a tight race for lieutenant governor against Republican incumbent Abel Maldonado, he will need to persuade voters that he is more than the Gay Marriage Mayor — and that they should give him a job he mocked as meaningless before Jerry Brown muscled him out of contention for governor last fall.

The apparent contradictions don’t stop at City Hall.

Newsom grew up in two worlds. He is a self-made son of a divorced mother who scratched his way from the lower middle class to the heights of San Francisco society as a wine merchant and restaurateur. His father, a retired state appellate court judge with deep roots in San Francisco’s Democratic establishment, is best friends with oil heir Gordon Getty, manages Getty’s family trust and has opened gilded doors for his son.

As a child, Newsom was whipsawed between competing realities: living with a mother who worked three jobs and vacationing with the Gettys, meeting the famous Leakeys in Africa or visiting Hudson Bay to see polar bears denning.

“Gordon Getty is someone who has very significantly shaped me,” Newsom said during an interview in his downtown campaign headquarters. But, he added, “My name is Newsom, not Getty. No trust funds in my life.”

Even Newsom’s good looks have been a mixed blessing. Like Cyrano’s nose, Newsom’s physical gifts — the tall, graceful silhouette, the Gordon Gekko hair, the electric white teeth — haven’t always served him well.

“People love to psychoanalyze Gavin,” said Mimi Silbert, a drug rehab pioneer who helped him through a personal crisis three years ago. “One, because of that upbringing. Two, just look at him. Here is this handsome guy who refuses to change the way he does his hair even though everyone in the world tortures him about it.”

In February 2004, a few weeks into his first mayoral term, Newsom became an instant hero to many when he abruptly began issuing marriage licenses to same-sex couples. In May 2008, after the California Supreme Court upheld the right of gays to marry, Newsom inadvertently gave opponents of gay marriage the sound bite of the year, declaring that gay marriage was coming “whether you like it or not!” Six months later, voters passed Proposition 8, the ballot measure that would amend the state Constitution to ban same-sex marriage.

“No one regrets that more than him,” said senior Newsom advisor Mike Farrah. “He was taken away by the moment.”

In 2007, Newsom’s personal life imploded in a sex and alcohol scandal around the time his first marriage collapsed. He had been drinking the night he arrived at a hospital to comfort the family of a fatally wounded police officer, according to news reports. He was spotted around town with an underage date, who was seen drinking at one social function they attended, the San Francisco Chronicle said. He admitted he had had an affair with his appointments secretary, who was married to his campaign manager and deputy chief of staff.

Newsom sought help from Silbert, founder of the Delancey Street Foundation, a highly regarded rehab center for hard-core drug addicts.

“I am not sure I would call him an alcoholic,” Silbert said. “But from Day One, I told him no more alcohol — and he stopped drinking.”

Newsom has left a trail of betrayed friends and colleagues, many of whom say they will never forgive him for the affair. The voters forgave him, though; they reelected him with 72% of the vote.

He has been groomed for higher office since he was appointed by San Francisco Mayor Willie Brown to the Parking and Traffic Commission in 1996. The following year, his politically connected father urged John Burton, then a Democratic state senator, to lobby Brown to appoint his son to the San Francisco Board of Supervisors, a body so diverse the position was jokingly called the “straight white male” seat.

Newsom went on to serve three more terms on the board before becoming mayor. His mentors have also included House Speaker Nancy Pelosi, to whom he is related by marriage, and Sen. Dianne Feinstein.

Should he become lieutenant governor, a low-profile, relatively powerless post, most Newsom observers say he will try to use the opportunity as a launching pad for higher office — governor, or perhaps U.S. senator. In the past, he has made no secret of his wish to be president, say many former associates.

While supporters see a creative thinker who has mastered the details of policy and is unafraid to tackle big issues, detractors charge that Newsom is a hypocrite who takes too much credit for the initiatives of others, spreads himself too thin and doesn’t keep his promises.

Newsom opposes offshore oil drilling and made that position the centerpiece of his first TV spot in this race; the lieutenant governor sits on a commission that oversees leasing of the state’s seabed. “We need to tell the oil companies, don’t mess with California, leave our coastline alone. It’s about time we took a stand,” he says in the ad.

But in a recent financial disclosure form, which bears Newsom’s signature, the mayor and his wife, Jennifer Siebel Newsom, reported that in August 2009 they invested between $10,000 and $100,000 in Transocean Inc., owner of the BP Deepwater Horizon drilling rig that exploded in the Gulf of Mexico last spring, killing 11 and causing one of the worst oil spills in U.S. history.

After the San Francisco Chronicle reported the investment, Newsom said through a spokesman that he was unaware of it. Later, the couple sold all of their energy-related holdings, including those in Transocean, and put the proceeds in a blind trust, his spokesman said.

Despite his considerable public charm, Newsom has a fractious relationship with the Board of Supervisors, almost none of whom consider him an ally.

“He is self-consumed, very lonely, very angry and remarkably indecisive,” said Aaron Peskin, who was president of the Board of Supervisors from 2005 to 2008. “If a member of the board came forward and said, ‘I am getting ready to introduce legislation,’” Peskin said, “I would say, ‘Don’t tell Newsom, he’ll rip it off.’”

Peskin is one of many who knock Newsom for failing to give proper credit to state Sen. Tom Ammiano, a San Francisco Democrat and former supervisor who championed universal healthcare for the city, a national first. More than 40,000 people are enrolled in the program, which requires employers with 20 or more workers to provide coverage. Newsom had opposed the mandated employer contributions that are a pivotal part of the law.

“The mayor has always given credit to Tom,” said his former press secretary, Peter Ragone.

The issue that vaulted Newsom into the mayor’s office was homelessness, a problem that has plagued all of the city’s recent mayors. His program, “Care Not Cash,” approved by voters, offered adults housing and support services in exchange for the lion’s share of their general assistance checks. The “tough love” approach alienated some on the city’s far left, who found it paternalistic.

About 2,700 adults have been housed, according to the city and advocates for the homeless. When he proposed the plan, Newsom said it could end homelessness in a decade, something experts said was unlikely absent a huge infusion of federal dollars.

Newsom boasts of having reduced the number of homeless San Franciscans by 12,000, but his critics say the figure is misleading.

“Homelessness has actually increased,” said Supervisor Chris Daly, a longtime Newsom antagonist who opposed the Care Not Cash program. “It’s not his fault,” — the economic downturn is the culprit—”but it happened during his tenure.”

It’s difficult to count the city’s fluid homeless population, said Jennifer Friedenbach, executive director of the local Coalition on Homelessness. At least 5,000 of the 12,000 people that Newsom says the city has helped were actually given bus tickets by police officers to leave town, she said.

“He likes to spin that as family reunification,” she said. “You can’t count that as housing people.”

A recent city report estimated the number of homeless at 13,500. About half are on the street, a number that has changed little in five years. This year, the family waiting list for shelters has tripled and is the highest it has been in about eight years, said Friedenbach; there has been a 50% increase in shelter requests for single homeless people.

Newsom has “done a good job of increasing housing,” Friedenbach said. “But he’s been very punitive toward homeless people in terms of the police and the use of the criminal justice system.”

She cited an upcoming city ballot measure pushed by Newsom that would make it illegal to sit or lie on San Francisco sidewalks between 7 a.m. and 11 p.m.

And Friedenbach said she won’t soon forgive the mayor for once promising a homeless family a computer and not coming through. In 2005, she took some parents and children to his City Hall conference room to lobby him to increase funding for homeless families. Eventually, he signed off on $2.3 million in funds. But the computer never materialized.

“They were literally coming in for weeks asking for the computer,” Friedenbach said. “I would call City Hall and say, ‘The kids are asking about the computer, what’s up?’ We sent him letters. No response.”

Mayoral spokesman Tony Winnicker said no one on the mayor’s staff recalled such a promise.

“Just like any of us,” said Jim Ross, who managed Newsom’s first mayoral campaign but like many former Newsom insiders is no longer a fan, “neither the worst things nor the best things that anyone says about him are accurate.”

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